To answer the OP, I would say start with s/t and then fan your way out backwards and forwards. If I had to pick his "best" albums I would say they are s/t, "Late Great" and "High Low and In Between" which are all on par with each other. But luckily since it's 2015 and I'm a free American I don't have to choose. All Townes material is great, and I would say all the studio albums are essential aside from the posthumous "In the beginning" LP which isn't bad but somewhat standard musically and lyrically. I'd say you need to acquire these:
For the sake of the song
Our Mother the Mountain
Live at the Old Quarter
S/T
Delta Momma Blues
Late, Great Townes Van Zandt
High Low and In Between
Nashville Sessions (this is the aborted '7 come 11' album that chronologically would have come after 'High Low' but was not released until the late 90s. Fantastic studio album, I think the only studio version of "Two Girls" is on this)
Flyin Shoes (worth it for the title track alone but the whole thing is wonderful. Has some of the same songs as '7 come 11' but different recordings)
At My Window (80s album, his voice getting more ragged, still prime Townes IMO. Also has some songs that were previously recorded for '7 come 11')
Rear View Mirror (live album, my introduction to the man, beautiful versions with violin accompaniment)
No Deeper Blue (90s album, a lot of people can't handle the production, but contains three of his all time best songs which are "Cowboy Junkies Lament", "Marie" and "A Song For". Also "Lovers Lament" and "The Hole")
after that I think the live albums "In Pain", "Rain on a Conga Drum", "Documentary", "Highway Kind" and "Absolutely Nothing" are all worth listening to.
I compiled a personal "best of" for a friends tape label a while back, there's a link to download it here:
https://www.wetransfer.com/downloads/e3b8fee7172ead2552d92b4ef95eb05f20151019220404/a710cc5d76427270a3789c11edf4c95a20151019220404/5e6d76It's unfortunately only split into two tracks, side A and side B. But here is the tracklisting:
side A
At My Window
Rex's Blues
Waiting Round to Die
Don't Take it too bad
Kathleen
No Place To Fall
I'll be here in the morning
Rake
Flyin Shoes
Two Girls
Pancho and Lefty
If I needed you
Highway Kind
Nothin'
side B
No Lonesome Tune
You are not needed now
No Deal
To Live is to Fly
High Low and In Between
Turnstyled, Junkpiled
Pueblo Waltz
Don't Let the Sunshine Fool Ya
Loretta
When She don't need me
Only Him or Me
Marie
A Song For
Cowboy Junkies Lament
The Hole
To address some other posts:
'For the sake of the song' is his first and is my favorite. It has quite a few of the same songs as 's/t' but the recordings are a little less produced, a little more intimate sounding, I think.
Surprised to read this because I think the exact opposite. The first album is likely my least favorite of his pre-80s material precisely because of the overdone production, the orchestration etc. It's much more tolerable on "Our Mother the Mountain", and then on s/t it's even more stripped down and heartfelt which is why I (and others) would suggest it as the best starting point.
The second album, "The Late Great Townes Van Zandt" is my favourite. Though I like all of the early albums.
That's his fifth album.
I too would recommend what some others have in checking out Billy Joe Shaver* (first three), Guy Clark (1st 2), Blaze Foley (all), DAC (first five Columbia albums, though a lot of his best songs are covers of guys like Guy Clark), and then there's Waylon Jennings "Honky Tonk Heroes" which is mostly Shaver covers, and so on and so on. But nothing touches Townes lyrically, nothing. It's transcendent stuff and at the risk of sounding like I'm blowing his corpse I'd say that his music sounds like it came straight from heaven and into the top of his skull and out through his hands. No other songwriter comes close.
If any of you find yourself near Galveston on New Years Day I highly recommend going to the annual Townes wake at the Old Quarter. Just people taking turns playing his songs all night long and getting buttfaced drunk. It's wonderful.
*even if he did rip off Townes' "Don't you take it too bad" for his song "It ain't nothin new babe"
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